Its not the right time of year riding in Indonesia december to february as its the rainy season there. I dont know exactly how bad it is - you got to do more research and talk to locals. Coming to Darwin March-April is probably ok-ish. The hot and humid season will be more or less over there. But June-July-August is winter in the southern part of Australia.
Indonesia is huge. Its traffic is extremly chaotic and jammed. Roads are narrow and often not in good conditions. Your average speed will in general not be more than 40-50 kms an hour. A daily run of maximum 300 kms is what you can expect.
You could probably still to Medan to Dili in 30 days if only riding - but you wouldnt see nothing of this country other than the road you have been riding and some million mopeds. My advice would be that you should not plan less than 60 days on that stretch to get some time off the bike to see and experience this extremely facinating country. I spent 3 months and one week doing the run from Medan to Dili but I did a months detour on Sulawesi.
Do get a 60 day visa in Malaysia before you go as a 30 day visa is only extendable one time and a 60 day visa is extendable 4 times.
You will love Indonesia if you choose to go there - and hate the traffic.
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